N,N-Dimethylglycine → HCID 42600096, compound

Participants

Reaction Conditions

Reaction Steps

Benzotriazol-1-yl-[bis(dimethylamino)methylene]oxonium tetrafluoroborate (115 mg) was added to a stirred suspension of 3-(1,3-benzoxazol-2-yl)-5-[3-(methoxymethyl)-1-piperidin-4-ylpyrazol-4-yl]pyridin-2-amine] (121 mg), 2-(dimethylamino)acetic acid (32.4 mg) and 4-methylmorpholine (0.066 ml) in NMP (1.5 ml) at 25° C. The mixture was stirred at 25° C. for 5 hours and purified by preparative HPLC using a Waters OBD reverse-phase column (C-18, 5 microns silica, 30 mm diameter, 150 mm length, flow rate of 40 ml/minute) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent to provide the title compound (101 mg, 69.0%). NMR Spectrum: (DMSOd6) 1.73-1.85 (m, 1H), 1.87-1.98 (m, 1H), 2.04-2.16 (m, 2H), 2.21 (s, 6H), 2.72-2.82 (m, 1H), 3.08 (d, 1H), 3.13-3.22 (m, 2H), 3.41 (s, 3H), 4.15-4.23 (m, 1H), 4.41 (s, 2H), 4.41-4.51 (m, 2H), 7.40-7.48 (m, 2H), 7.66 (bs, 2H), 7.78 (dd, 1H), 7.84 (dd, 1H), 8.23 (s, 1H), 8.43 (d, 1H), 8.50 (d, 1H); Mass spectrum: M+H+ 490.

Provenance & Evidence